Synthesis of tert-butylbenzene

Preparation of tert-butylbenzene (2-methyl-2-phenylpropane)

The tert-butyl chloride required for the reaction is prepared by shaking vigorously in a separatory funnel a mixture of 50 ml of tert-butyl alcohol and 250 ml of concentrated hydrochloric acid. After agitating very thoroughly for 10 minutes, the conversion should be complete and the lower acid layer should be perfectly clear. The tert-butyl chloride layer is carefully separated, dried the over calcium chloride, and purified by distillation, yielding, 45-50 g of tert-butyl chloride, which boils at 50-51° C.

Preparation of tert-butylbenzene (2-Methyl-2-phenylpropane)

Preparation of tert-butylbenzene (2-methyl-2-phenylpropane)

The preparation of tert-butylbenzene by the Friedel and Crafts reaction is best carried out in a 1 liter long-necked, round-bottomed flask which can be used later for steam distillation and which is fitted with a mechanical stirrer and a dropping funnel fitted into a three-way addition tube.

A glass apparatus for the preparation of tert-butylbenzene

A glass apparatus for the preparation of tert-butylbenzene

By applying a very gentle suction, the hydrogen chloride can be drawn into the trap and it is not necessary to use a gas seal for the stirrer. 50 g of tert-butyl chloride are placed in the dropping funnel and a mixture of 50 g of anhydrous aluminum chloride and 175 ml of dry benzene are introduced in the reaction flask. The reaction flask is immersed in a salt-ice bath while stirring, 2-3 ml of the tert-butyl chloride is added dropwise from the dropping funnel in order to prevent the benzene from freezing. The tert-butyl chloride in portions is added over a period of 6 hours, with constant stirring and keeping the mixture at a temperature of 0-5° C. After all tert-butyl chloride have been added the stirring is continued for additional hour. Then in small portions 150-200 g of ice are added while maintaining external cooling and stirring of the reaction flask. 50-100 ml of cold water are added to complete the decomposition of the intermediate product and then the reaction mixture is steam distilled. After separating the upper layer of benzene and tert-butylbenzene, the water layer is extracted with ether, the ethereal solutions were combined with the benzene and tert-butylbenzene solution. The extract is dried thoroughly over calcium chloride and fractionally distilled twice, using a fractionating column. In the second distillation, the fraction boiling at 164-168° C is retained. The pure tert-butylbenzene boils at 167° C. The yield of tert-butylbenzene is 35-45 g.

Experiments in Organic Chemistry, L. F. Fieser, 180-181, 1941

IUPAC Name

tert-butylbenzene

InChI

InChI=1S/C10H14/c1-10(2,3)9-7-5-4-6-8-9/h4-8H,1-3H3

InChI Key

YTZKOQUCBOVLHL-UHFFFAOYSA-N

Canonical SMILES

CC(C)(C)C1=CC=CC=C1

MeSH Synonyms

1-bromo-4-tert-butylbenzene, t-butylbenzene, tert-butylbenzene

Depositor-Supplied Synonyms

tert-Butylbenzene, 98-06-6, T-BUTYLBENZENE, 2-Methyl-2-phenylpropane, Benzene, tert-butyl-, Pseudobutylbenzene, Benzene, (1,1-dimethylethyl)-, Dimethylethylbenzene, Phenyltrimethylmethane, Trimethylphenylmethane, (tert-butyl)benzene, 1,1-Dimethylethylbenzene, tert-butyl-benzene, tertiary-Butylbenzene, NSC 6557, Dimethylethylbenzene (VAN), HSDB 5315, YTZKOQUCBOVLHL-UHFFFAOYSA-N, EINECS 202-632-4, SBB040882, AI3-00118, t-butyl benzene, tert.butylbenzene, 4-t-butylbenzene, tert-butyl benzene, Benzene, t-butyl-, ACMC-20ajki, AC1L1OLJ, AC1Q1HYI, 1,1-Dimethylethyl-benzene, UN 2709 (Related), UNII-M1R2NME7S2, DSSTox_CID_27138, DSSTox_RID_82145, M1R2NME7S2, DSSTox_GSID_47138, B90602_ALDRICH, KSC490M5R, CHEMBL1797277, 19640_FLUKA, 19650_FLUKA, CTK3J0658, NSC6557, MolPort-000-872-044, NSC-6557, STR09192, Tox21_300540, AR-1L5860, STL264211, ZINC01693606, AKOS000120008, MCULE-8566444437, RP20161, RTR-030281, TRA0063605, WLN: 1X1 & 1 & R, CAS-98-06-6, NCGC00248088-01, NCGC00254436-01, AJ-30215, AK116992, AN-24475, K762, KB-11855, L690, LS-29364, DB-057706, ST2413956, TR-030281, B0715, FT-0631505, S0661, ST50214479, A845799, I01-0112, InChI=1/C10H14/c1-10(2,3)9-7-5-4-6-8-9/h4-8H,1-3H

Removed Synonyms

Dimethyl ethyl benzene, 2-Phenyl-2-methylpropane, Benzene,1-dimethylethyl)-, 4-Chloro-7-nitrobenzofurazan, CID7366, 2028-11-7

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *